CN106045990A - Phenanthroline derivative and use thereof - Google Patents
Phenanthroline derivative and use thereof Download PDFInfo
- Publication number
- CN106045990A CN106045990A CN201610055491.9A CN201610055491A CN106045990A CN 106045990 A CN106045990 A CN 106045990A CN 201610055491 A CN201610055491 A CN 201610055491A CN 106045990 A CN106045990 A CN 106045990A
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- China
- Prior art keywords
- substituted
- unsubstituted
- layer
- coffee quinoline
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 title 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 84
- 241001597008 Nomeidae Species 0.000 claims abstract description 41
- 230000027756 respiratory electron transport chain Effects 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims description 57
- 230000005611 electricity Effects 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 230000004888 barrier function Effects 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000001725 pyrenyl group Chemical group 0.000 claims description 6
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 claims 1
- 230000005284 excitation Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 60
- 239000011799 hole material Substances 0.000 description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- -1 quinoline (bis-phenanthroline) compound Chemical class 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000005540 biological transmission Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 150000002460 imidazoles Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000008569 process Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000007872 degassing Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000004020 luminiscence type Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000004776 molecular orbital Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AQLZGOSDTNLEIC-UHFFFAOYSA-N 10,10-dimethyl-12-(4-(pyren-1-yl)phenyl)-10h-indeno[1,2-b]triphenylene Chemical group C1=C2C(C3=CC=C(C=C3)C3=CC(C4=C5C=C6C7=CC=CC=C7C7=CC=CC=C7C6=CC5=CC4=C3)(C)C)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 AQLZGOSDTNLEIC-UHFFFAOYSA-N 0.000 description 1
- JXPNBVDZCUHHOL-UHFFFAOYSA-N 2-(4-bromophenyl)-1-[4-(10-naphthalen-1-ylanthracen-9-yl)phenyl]benzimidazole Chemical compound BrC1=CC=C(C=C1)C1=NC2=C(N1C1=CC=C(C=C1)C=1C3=CC=CC=C3C(=C3C=CC=CC=13)C1=CC=CC3=CC=CC=C13)C=CC=C2 JXPNBVDZCUHHOL-UHFFFAOYSA-N 0.000 description 1
- AKBLCLCWSIYBSM-UHFFFAOYSA-N 2-(4-phenylphenyl)-5-[9-[5-(4-phenylphenyl)-1,3,4-oxadiazol-2-yl]-1,10-phenanthrolin-2-yl]-1,3,4-oxadiazole Chemical compound C1=CC=CC=C1C1=CC=C(C=2OC(=NN=2)C=2N=C3C4=NC(=CC=C4C=CC3=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 AKBLCLCWSIYBSM-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
- RLPAWKJLZUFLCR-UHFFFAOYSA-N 4-(4-aminophenyl)-3-naphthalen-1-yl-n,n-diphenylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC2=CC=CC=C12 RLPAWKJLZUFLCR-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- DFHNGUMPLOMIQA-UHFFFAOYSA-N BrC=1C2=CC=CC=C2C(=C2C=CC=CC12)Br.BrC=1C2=CC=CC=C2C(=C2C=CC=CC12)Br Chemical compound BrC=1C2=CC=CC=C2C(=C2C=CC=CC12)Br.BrC=1C2=CC=CC=C2C(=C2C=CC=CC12)Br DFHNGUMPLOMIQA-UHFFFAOYSA-N 0.000 description 1
- RPSFVIMXVKMKGT-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=CC=C(C=C1)N1C(=NC2=C1C=CC=C2)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C Chemical compound C1(=CC=CC2=CC=CC=C12)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=CC=C(C=C1)N1C(=NC2=C1C=CC=C2)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C RPSFVIMXVKMKGT-UHFFFAOYSA-N 0.000 description 1
- GBIMOPJDFZSVNV-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=CC=C(C=C1)N1C(=NC2=C1C=CC=C2)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C Chemical compound C1(=CC=CC=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=CC=C(C=C1)N1C(=NC2=C1C=CC=C2)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C GBIMOPJDFZSVNV-UHFFFAOYSA-N 0.000 description 1
- GUNIQBVDEQQVGH-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=CC=C(C=C1)N1C(=NC2=C1C=CC=C2)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C Chemical compound C1=C(C=CC2=CC=CC=C12)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=CC=C(C=C1)N1C(=NC2=C1C=CC=C2)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C GUNIQBVDEQQVGH-UHFFFAOYSA-N 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- MWIFXQRDVQPSNE-UHFFFAOYSA-N N1=CC=CC2=CC=C3C=CC=NC3=C12.N1=CC=CC2=CC=CC=C12 Chemical compound N1=CC=CC2=CC=C3C=CC=NC3=C12.N1=CC=CC2=CC=CC=C12 MWIFXQRDVQPSNE-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- FEJIZDCZCSUUAH-UHFFFAOYSA-N aniline 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline Chemical compound CC1(OB(OC1(C)C)C1=CC=C(C=C1)N)C.NC1=CC=CC=C1 FEJIZDCZCSUUAH-UHFFFAOYSA-N 0.000 description 1
- DMMLYDCVMZEUMT-UHFFFAOYSA-N benzo[h]cinnoline Chemical compound C1=NN=C2C3=CC=CC=C3C=CC2=C1 DMMLYDCVMZEUMT-UHFFFAOYSA-N 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
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- 230000000052 comparative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
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- 239000010408 film Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 102000057593 human F8 Human genes 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- VZOPRCCTKLAGPN-ZFJVMAEJSA-L potassium;sodium;(2r,3r)-2,3-dihydroxybutanedioate;tetrahydrate Chemical compound O.O.O.O.[Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O VZOPRCCTKLAGPN-ZFJVMAEJSA-L 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229940047431 recombinate Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 229940074446 sodium potassium tartrate tetrahydrate Drugs 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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Abstract
The present invention relates to a kind of coffee quinoline derivants, and structure is by shown in formula (I), wherein the definition of Ar, m, n, p and R1 to R4 are identical as description herein. The present invention is also related to a kind of electromechanical excitation device, and aforementioned coffee quinoline derivant is used to stop electron transfer layer or electron transfer layer as electric hole, can express excellent efficiency, such as: it reduces driving voltage and power dissipation, increase efficiency and half-life.
Description
Technical field
It is said that in general, the present invention is about a kind of coffee quinoline derivant and a kind of organic electric shock utilizing aforementioned coffee quinoline derivant
(the most organic EL) light-emitting device.More specifically, the present invention has formula (I) chemical constitution about one
Coffee quinoline derivant, and a kind of use this coffee quinoline derivant with formula (I) structure to stop electric transmission material as electricity hole
Material (hole blocking electron transport material, HBETM) and electron transport material (electron
Transport material, ETM) organic el device.
Background technology
Organic electric-excitation luminescent (organic EL) is a kind of light emitting diode (LED), and wherein luminescent layer is by organic compound
The film that thing is made, it can emit beam under corresponding electric current.The luminescent layer of organic compound is located in two electrodes
Between.Organic EL due to its high illumination, low weight, Low-profile, from illumination without backlight, low-power consumption,
Wide viewing angle, high-contrast, manufacture method be simple and response time quick characteristic and be applied in flat faced display.
Observe for the first time the phenomenon of organic material electroluminescence be generation nineteen fifty in early days by An Deliebei nano this
(Andre Bernanose) and colleague are carried out in France Nancy. university (Nancy-University).New York University
The Martin Pu primary (Martin Pope) of (New York University) and its colleague are in 1963 the most under vacuo
Unidirectional current (DC) electroluminescence is observed on the single pure crystal of the anthracene doped with aphthacene.
First diode apparatus in 1987 by the Deng Qingyun (Ching of Eastman Kodak Company (Eastman Kodak)
W.Tang) delivered with Shi Diwenfansi Rec (Steven Van Slyke).The use of this device has separately positioned
Electricity hole transport layer and the double-decker of electron transfer layer so that running voltage reduces and improves efficiency, when leading current
Organic EL research in generation and device produce.
Typically, organic EL is to be made up of the organic material layer between two electrodes, and it includes the transmission of electricity hole
Layer (hole transporting layer, HTL), luminescent layer (emitting layer, EML), electron transfer layer
(electron transporting layer, ETL).The fundamental mechanism of organic EL relates to the note of carrier (carrier)
Enter, the transmission of carrier, recombinate and form exciton (exciton) with luminescence.When external voltage is applied to organic light emission dress
When putting, electronics and electricity hole are injected from negative electrode and anode respectively, and electronics will be injected into minimum vacant molecular orbital from negative electrode
In (lowest unoccupied molecular orbital, LUMO), and electricity hole will be injected into the highest taking from anode
In molecular orbital (highest occupied molecular orbital, HOMO).When electrons and holes is in luminescent layer
During restructuring, form exciton and luminescence subsequently.When light emitting molecule absorb energy and when reaching excited state, according to electronics and
The spin combination in electricity hole, exciton can be in singlet state or triplet.The exciton of 75% is formed by the restructuring of electronics and electricity hole
And reach triplet excited state.It is spin forbidden (self forbidden) from triplet decay.Therefore, fluorescence electric shock
Light-emitting device only has the internal quantum of 25%.Compared to fluorescence el light emitting device, phosphorescence organic light-emitting diodes
Pipe utilizes spin-orbital interaction (spin-orbit interaction) can promote the system between singlet state and triplet
Between pass through (intersystem crossing), thus obtain from singlet state and the luminescence of triplet, and be electrically excited
The internal quantum of electro-optical device rises to 100% from 25%.
In recent years, Anda professor (Adachi) and colleague's research and development one thereof combine thermally activated delayed fluorescence (thermally
Activated delayed fluorescence, TADF) mechanism novel fluorescence organic el device, it is by instead
To between system, pass through (reverse intersystem crossing, RISC) mechanism, the triplet of spin forbidden is swashed
Son converts to singlet state energy rank the high efficiency one formed to obtain exciton and has promising mode.
Triplet and singlet excitons all can be utilized by the organic EL of phosphorescence.Due to compared with singlet excitons, triplet
Exciton has longer vital stage and diffusion length, the organic EL of phosphorescence it is generally required to luminescent layer (emitting layer,
EML) and between electron transfer layer (electron transporting layer, ETL), extra barrier layer, electric hole is set
(hole blocking layer, HBL) or there is the electron transfer layer (being HBETL) of electric hole blocking capability, rather than
Typical ETL.The purpose using HBL or HBETL is to limit the restructuring between electric hole and the electronics injected,
And make the exciton being positioned at EML generation present lax (relaxation), thus improved the efficiency of device.
In order to meet these effects, electricity hole barrier material must have be adapted to block electricity hole from EML transmission to ETL,
And by electronics from ETL be sent to EML HOMO Yu LUMO can rank, additionally need material to possess well
Heat stability and electrochemical stability.
Nowadays, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-dimethyl-4,7-di
Phenyl-1,10-phenanthroline, BCP), bathophenanthroline (bathophenanthroline, Bphen) has been used as phosphorus
The typical material of HBL and HBETL in light OLED field.But, compared to Bphen and BCP, coffee quinoline spreads out
Biology has relatively low glass transition temperature (Tg) (such as: the Tg of Bphen is 55 DEG C, and BCP is 65 DEG C), relatively
Low cracking temperature (Td) is (such as: Bphen weight loss when 240 DEG C is less than 0.5%；BCP is weight when 260 DEG C
Amount loss is less than 0.5%), and cracking temperature is relevant with heat resistance.This kind of material is difficult to operate in depositing operation,
And the light-emitting device stability prepared is low, the half-life is short.U.S. Patent No. 7,119,204 relates to passing as electronics
A series of coffee quinoline derivants being substituted of defeated material.U.S. Patent No. 7,282,586 relates to a kind of electronics that is used as and passes
The specific coffee quinoline derivant of defeated material, is 2, double (5-(biphenyl-4-base)-1,3, the 4-oxadiazoles-2-base)-1 of 9-, 10-phenanthroline
(2,9-bis (5-(biphenyl-4-yl)-1,3,4-oxadiazol-2-yl)-1,10-phenanthroline), and with prior art
BCP material is compared, and it is 2000cd/m in brightness2Time, driving voltage is down to 7V from 8V, and is reached higher
Current efficiency.U.S. Patent No. 7,754,348 relates to the substituted coffee of a series of 2,9-as electron transport material
Quinoline derivant, if comparative example 1-3 and Alq carried with this case3Compare down, when driving voltage is 5V, aforementioned
2,9-substituted coffee quinoline derivant then reaches longer operation lifetime and higher brightness (luminance).U.S. Patent No.
7,982, No. 213 relate to a series of through aryl substituted coffee quinoline derivant, and organic EL phosphorescence light-emitting device uses this
Stop that electron transfer layer can provide high efficiency, high brightness and height long-term through aryl substituted coffee quinoline derivant as electricity hole
Tolerance level (long-term durability).U.S. Patent No. 8,114,529 relates to a series of having double coffee quinoline
(bis-phenanthroline) compound of structural framework, utilizes this coffee quinoline compounds to stop electric transmission as electricity hole
Layer, prepared organic EL phosphorescence light-emitting device has low driving voltage and well tolerable property.
Sustainable existence can effectively transmit electronics and can stop electricity hole, can have again good thermal stability and high-luminous-efficiency
The demand of organic EL Material.According to above-mentioned reason, these that it is an object of the invention to solve prior art are asked
Topic, and provide heat stability, high-luminous-efficiency, high brightness and long half-lift the time in terms of excellent the sending out of performance
Electro-optical device.The present invention relates to one and there is the novel coffee quinoline derivant of formula (I) structure, may be used as electricity hole and stop electricity
Son transmission material (HBETM), electron transport material (ETM), it has good charge carrier mobility with excellent
Operational durability, it is possible to reduce driving voltage and power consumption, increases efficiency and the half-life length of organic el device.
Summary of the invention
The present invention provides a kind of coffee quinoline (phenanthroline) derivant, and it can be used for the electric hole in organic el device
Stop electron transport material (hole blocking electron transport material, HBETM) or electric transmission material
Material (electron transport material, ETM).This type of coffee quinoline derivant can overcome lacking of the material of prior art
Lose, such as inefficient, the half-life is short and the problem of high power consumption.
It is an object of the present invention to provide a kind of electric hole that can be used in organic el device and stop electric transmission material
Material (HBETM) or the coffee quinoline derivant of electron transport material (ETM).
The present invention has economic advantages on industrial practice.According to the present invention, relate to a kind of for organic el device
Coffee quinoline derivant.Aforementioned coffee quinoline derivant can be by represented by lower formula (I):
Wherein L represents the arlydene being substituted or being unsubstituted with 6 to 30 ring carbon atoms；M represents 0
To the integer of 6, n represents the integer of 0 to 4, and p represents the integer of 0 to 4；Ar is for having 6 to 50 ring carbon
The aryl being substituted or being unsubstituted of atom, aforesaid aryl can be phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, bend
Base or other alternative group；R1To R4Independently selected from by hydrogen atom, the warp with 1 to 20 carbon atom
The alkyl replaced or be unsubstituted, the aryl being substituted or being unsubstituted with 6 to 30 carbon atoms and tool
The group being made up of the heteroaryl being substituted or being unsubstituted of 3 to 30 carbon atoms.
Another object of the present invention is to, it is provided that a kind of organic el device, it includes being made up of negative electrode and anode
Electrode, and at least include the material layer of coffee quinoline derivant as shown in formula (I), and aforesaid at least one material
Layer is arranged at this between negative electrode and the anode of electrode.
Replace it is preferred that aforesaid at least one material layer can be electron transfer layer, electricity hole stop electron transfer layer or other tools
Layer for function.
Accompanying drawing explanation
Fig. 1 is the schematic diagram of an embodiment of the organic el device of the present invention.
6 transparency electrode 7 electricity hole implanted layers
8 electricity hole transport layer 9 luminescent layers
10 electricity barrier layer, hole 11 electron transfer layers
12 electron injecting layer 13 metal electrodes
Detailed description of the invention
The present invention is intended to probe into aforesaid coffee quinoline derivant and use the organic el device of this coffee quinoline derivant.Under
Literary composition will provide the detailed description of production, structure and key element so that the present invention can be understood fully.Obviously the present invention
Application be not limited to specific detail familiar to those skilled in the art.On the other hand, the common elements of common general knowledge
It is not described in detail in the present invention with process, and the present invention should not produced unnecessary restriction.Now will hereinafter
It is more fully described some preferred embodiments of the present invention.But, should be recognized by, the present invention can be except clearly retouching
Extensive various other embodiments outside the embodiment stated is put into practice, i.e. it is real that the present invention can also be widely used in other
Execute example, and specified in such as claim in addition to, the scope of the present invention is the most clearly limited.
Addressing a kind of coffee quinoline derivant herein, it has the chemical constitution shown in following formula (I).In a preferred embodiment
In, aforementioned coffee quinoline derivant can be used for the electric hole of organic el device and stops electron transport material or electron transport material.
Wherein L represents the arlydene being substituted or being unsubstituted with 6 to 30 ring carbon atoms；M represent 0 to
The integer of 6, n represents the integer of 0 to 4, and p represents the integer of 0 to 4；Ar is former for having 6 to 50 ring carbon
The aryl being substituted or being unsubstituted of son, aforesaid aryl can be phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl
Or other alternative group；R1To R4Independently selected from by hydrogen atom, the warp with 1 to 20 carbon atom
The alkyl replaced or be unsubstituted, the aryl being substituted or being unsubstituted with 6 to 30 carbon atoms and tool
The group being made up of the heteroaryl being substituted or being unsubstituted of 3 to 30 carbon atoms.
In a preferred embodiment, according to the coffee quinoline derivant shown in formula (I), Ar has selected from by general formula
A kind of structure in the group formed:
In a preferred embodiment, this coffee quinoline derivant can be further by shown in following formula (II):
Wherein L represents the arlydene being substituted or being unsubstituted with 6 to 30 ring carbon atoms；M represent 0 to
The integer of 6, n represents the integer of 0 to 4, and p represents the integer of 0 to 4；Ar is former for having 6 to 50 ring carbon
The aryl being substituted or being unsubstituted of son, aforesaid aryl can be phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl
Or other alternative group；R1To R4Independently selected from by hydrogen atom, the warp with 1 to 20 carbon atom
The alkyl replaced or be unsubstituted, the aryl being substituted or being unsubstituted with 6 to 30 carbon atoms and tool
The group being made up of the heteroaryl being substituted or being unsubstituted of 3 to 30 carbon atoms.
In a preferred embodiment, according to the coffee quinoline derivant shown in formula (II), Ar has selected from by general formula
A kind of structure in the group formed:
In a preferred embodiment, in the group that the structure of this coffee quinoline derivant can be made up of general formula wherein
Shown in a kind of:
On the other hand, addressing a kind of OLED herein, it can include be made up of negative electrode and anode
To electrode, and this material layer to comprising at least one amine derivative as herein described between electrode.Refer to shown in Fig. 1,
In a preferred embodiment, this kind of OLED can include transparency electrode 6, electricity hole implanted layer 7, electricity hole
Transport layer 8, electronic barrier layer 9, luminescent layer 10, electron transfer layer 11, electron injecting layer 12 and metal electrode
13.In this device, electricity hole implanted layer 7 is arranged between transparency electrode 6 and metal electrode 13, electricity hole transport layer
8 are arranged between electron injecting layer 7 and metal electrode 13, and electronic barrier layer 9 is arranged at electricity hole transport layer 8 and gold
Belonging between electrode 13, luminescent layer 10 is arranged between electronic barrier layer 9 and metal electrode 13, electron transfer layer 11
Be arranged between luminescent layer 10 and metal electrode 13, and electron injecting layer 12 be arranged at electron transfer layer 11 with
Between metal electrode 13.Additionally, in a preferred embodiment, luminescent layer 10 can send phosphorescence, fluorescence, or other
The light of generation can be electrically excited through organic material；More preferably, luminescent layer 10 can send phosphorescence or fluorescence.
Illustrate the detailed preparation of coffee quinoline derivant in the present invention below by way of exemplary embodiment, but the invention is not restricted to this
Etc. exemplary embodiment.The preparation of some embodiments of coffee quinoline derivant in the embodiment 1-3 present invention.Embodiment 4 is opened up
Show the manufacture of organic el device, and the I-V-B of organic el device test report, half-life.
Embodiment 1: the synthesis of compound EX1
The synthesis bromo-10-of 9-(naphthalene-1-base) anthracene (9-bromo-10-(naphthalen-1-yl) anthracene)
By the 9,10-dibromoanthracene (9,10-dibromoanthracene) of 40g (119mmol), 20.5g (119mmol)
1-naphthalene boronic acids (naphthalen-1-ylboronic acid), the tetrakis triphenylphosphine palladium (Pd (PPh of 1.38g (1.2mmol)3)4)、
After the 2M sodium carbonate of 120ml, 200ml ethanol and the mixing of 600ml toluene, process also through degassing (degas)
It is placed under nitrogen environment, within 12 hours, reacts with 100 DEG C of heating subsequently.Mixture cooling after reaction is completed
To room temperature, utilize ethyl acetate and water to extract organic layer, then utilize anhydrous magnesium sulfate to be dried organic layer and
Forming residue after removing solvent, residue is purified via silica-filled col-umn chromatography, it is thus achieved that 19.2g
The product (50mmol) of yellow solid, productivity is 42%.
Synthesis 4-(10-(naphthalene-1-base) anthracene-9-base) aniline (4-(10-(naphthalen-1-yl) anthracen-9-yl) aniline)
By the bromo-10-of 9-(naphthalene-1-base) anthracene of 30g (52.2mmol), 4-(the 4,4,5,5-tetramethyl of 13.7g (62.6mmol)
-1,3,2-dioxaborolane-2-base) aniline (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
Aniline), the tetrakis triphenylphosphine palladium of 0.6g (0.52mmol), the 2M sodium carbonate of 52ml, 150ml ethanol and
After the mixing of 450ml toluene, process through degassing and be placed under nitrogen environment, within 12 hours, enter with 100 DEG C of heating subsequently
Row reaction.Mixture after reaction being completed is cooled to room temperature, utilizes ethyl acetate and water to extract organic layer, then will
Organic layer forms residue after utilizing anhydrous magnesium sulfate to be dried and removing solvent, and residue is filled out via silicon dioxide
The col-umn chromatography filled is purified, it is thus achieved that the product (32.3mmol) of 12.8g yellow solid, and productivity is 62%.
Synthesis N-(4-(10-(naphthalene-1-base) anthracene-9-base) phenyl)-2-nitroaniline (N-(4-(10-(naph
-thalene-1-yl)anthracen-9-yl)phenyl)-2-nitroaniline)
By 4-(10-(naphthalene-1-base) anthracene-9-base) aniline of 10g (25.3mmol), the 1-iodo-2-nitre of 6.3g (25.3mmol)
Base benzene (1-iodo-2-nitrobenzene), the acid chloride (Pd (OAc) of 56.7mg (0.25mmol)2)、4.86mg
(50.6mmol) sodium tert-butoxide (sodium tert-butoxide), the mixture of 400ml o-Dimethylbenzene (O-xylene) pass through de-
Gas disposal is placed under nitrogen environment, within 12 hours, reacts with 140 DEG C of heating subsequently.Mixing after reaction is completed
Compound is cooled to room temperature, utilizes ethyl acetate and water to extract organic layer, then organic layer utilizes anhydrous magnesium sulfate carry out
Forming residue after being dried and remove solvent, residue is purified via silica-filled col-umn chromatography, it is thus achieved that
The product (8.6mmol) of 4.44g yellow solid, productivity is 34%.
Synthesis N1-(4-(10-(naphthalene-1-base) anthracene-9-base) phenyl) benzene-1,2-diamidogen (N1-(4-(10-(naph-thalen-1-yl)
anthracen-9-yl)phenyl)benzene-1,2-diamine)
By N-(4-(10-(naphthalene-1-base) anthracene-9-base) the phenyl)-2-nitroaniline of 10g (19.3mmol), 3.24g (58mmol)
Iron powder, 200ml ethanol mixture through degassing process be placed under nitrogen environment, subsequently with 80 DEG C of heating
30 minutes, add the hydrochloric acid of 12.1ml 37.5% (96.5mmol) subsequently, then within 12 hours, carry out with 80 DEG C of heating
Reaction.Mixture reaction completed is cooled to room temperature.Add 13ml ammonia solution (ammonia solution),
After the extremely cooling of the sodium potassium tartrate tetrahydrate (potassium sodium tartrate) of 21.8g (77.2mmol) and the water of 600ml
Mixture, stirs 30 minutes.Utilize dichloromethane and water to extract organic layer, then organic layer is utilized anhydrous slufuric acid
Magnesium forms residue after being dried and remove solvent, and residue carries out pure via silica-filled col-umn chromatography
Change, it is thus achieved that the product (7.8g, 16mmol) of brown solid, productivity is 83%.
Synthesis 2-(4-bromophenyl)-1-(4-(10-(naphthalene-1-base) anthracene-9-base) phenyl)-1H-benzo [d] imidazoles (2-(4-
bromophenyl)-1-(4-(10-(naphthalen-1-yl)anthracen-9-yl)phenyl)-1H-benzo[d]imidazole)
By N1-(4-(10-(naphthalene-1-base) anthracene-9-base) phenyl) benzene-1,2-diamidogen of 10g (20.5mmol),
The bromo-benzaldehyde of the 4-(4-bromo-benzaldehyde) of 4.56g (24.7mmol), 782mg (4.1mmol) to benzene
Sulphur formic acid (p-toluenesulfonic acid), the mixture of 200ml dry toluene process through degassing and are placed in nitrogen
Under environment, within 12 hours, react with 110 DEG C of heating subsequently.Mixture after reaction being completed is cooled to room temperature,
Dichloromethane and water is utilized to extract organic layer, then after organic layer is utilized anhydrous magnesium sulfate to be dried and removes solvent
Forming residue, residue is purified via silica-filled chromatographic analysis, it is thus achieved that 3.74g yellow solid
Product (5.7mmol), productivity is 28%.
Synthesis 1-(4-(10-(naphthalene-1-base) anthracene-9-base) phenyl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane
0-2-yl) phenyl)-1H-benzo [d] imidazoles (1-(4-(10-(naphthalen-1-yl) anthracen-9-yl) phenyl)-2-
(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole)
By 2-(4-bromophenyl)-1-(4-(10-(naphthalene-1-base) anthracene-9-base) phenyl)-1H-benzo [d] imidazoles of 5g (7.67mmol),
The 4,4,4' of 2.14g (8.4mmol), 4', 5,5,5', 5'-prestox-2,2'-join (1,3,2-dioxaborolane)
(4,4,4', 4', 5,5,5', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane), the four (triphens of 177mg (0.15mmol)
Base phosphine) palladium, the potassium acetate (potassium acetate) of 1.5g (15.5mmol), 100ml1,4-dioxanes (1,4-dioxane)
Mixture through degassing process be placed under nitrogen environment, 100 ° of heating subsequently are reacted for 12 hours.Will be anti-
Mixture after should completing is cooled to room temperature, utilizes ethyl acetate and water to extract organic layer, then organic layer is utilized nothing
Water magnesium sulfate forms residue after being dried and remove solvent, and residue enters via silica-filled col-umn chromatography
Row purification, it is thus achieved that the product (4.4mmol) of 3.1g yellow solid, productivity is 58%.
Synthesis compound EX1
By 3g (8.2mmol) 2-chloro-4,7-diphenyl-1,10-coffee quinoline (2-chloro-4,7-diphenyl-1,10-
Phenanthroline), 6.28g (9mmol) 1-(4-(10-(naphthalene-1-base) anthracene-9-base) phenyl)-2-(4-(4,4,5,5-tetramethyl
-1,3,2-dioxaborolane-2-base) phenyl)-1H-benzo [d] imidazoles, 189mg (0.16mmol) four (triphenylphosphine)
Palladium, 8.2g2M sodium carbonate (Na2CO3), the mixture of 40ml ethanol and 120ml toluene process juxtaposition through degassing
Under nitrogen environment, within 12 hours, react with 100 DEG C of heating subsequently.Mixture after reaction being completed is cooled to
Room temperature, utilizes dichloromethane and water to extract organic layer, then utilizes anhydrous magnesium sulfate to be dried organic layer and remove
Forming residue after solvent, residue is purified via silica-filled col-umn chromatography, it is thus achieved that 4.8g yellow
The EX1 (5.3mmol) of solid, shaped, productivity is 65%.MS(m/z,FAB+): 902.8；1H NMR(CDCl3,
500MHz): chemical shift (ppm) 8.69 (d, 2H), 8.49 (d, 2H), 8.23 (s, 1H), 8.17～8.11 (d, 2H),
7.89～7.83 (m, 4H), 7.80～7.68 (m, 6H), 7.65～7.49 (m, 14H), 7.45～7.41 (m, 2H), 7.40～7.27 (m,
9H)。
Embodiment 2: the synthesis of compound EX6
Synthesis 4,7-diphenyl-2-(4-(1-(4-(10-phenylanthracene-9-base) phenyl)-1H-benzo [d] imidazoles-2-base) benzene
Base)-1,10-coffee quinoline (4,7-diphenyl-2-(4-(1-(4-(10-phenylanthracen-9-yl) phenyl)-1H-benzo [d]
imidazol-2-yl)phenyl)-1,10-phenanthroline)
Except with 1-(4-(10-(phenylanthracene-9-base) phenyl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-
Base) phenyl)-1H-benzo [d] imidazoles (1-(4-(10-phenylanthracen-9-yl) phenyl)-2-(4-(4,4,5,5-
Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-1H-benzo [d] imidazole) replace 1-(4-(10-(naphthalene
-1-base) anthracene-9-base) phenyl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-base) phenyl)-1H-benzo [d]
Imidazoles, remaining step is all identical with the synthetic method described in embodiment 1, it is thus achieved that 4.3g product (EX6), productivity is
62%.MS(m/z,FAB+): 852.8；1H NMR(CDCl3, 500MHz): chemical shift (ppm) 8.68 (d,
2H), 8.50 (d, 2H), 8.25 (s, 1H), 8.19～8.13 (d, 2H), 7.91～7.82 (m, 4H), 7.78～7.68 (m,
6H), 7.65～7.48 (m, 12H), 7.46～7.42 (m, 2H), 7.40～7.28 (m, 9H).
Embodiment 3: the synthesis of compound EX12
Synthesis 2-(4-(1-(4-(10-(naphthalene-2-base) anthracene-9-base) phenyl)-1H-benzo [d] imidazoles-2-base) phenyl)-4,7-hexichol
Base-1,10-coffee quinoline (4,7-diphenyl-2-(4-(1-(4-(10-phenylanthracen-9-yl) phenyl)-1H-benzo [d]
imidazol-2-yl)phenyl)-1,10-phenanthroline)
Except with 1-(4-(10-(naphthalene-2-base) anthracene-9-base) phenyl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxo bora ring penta
Alkane-2-base) phenyl)-1H-benzo [d] imidazoles) (1-(4-(10-(naphthalene-2-yl) anthracen-9-yl) phenyl)-
2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-1H-benzo [d] imidazole) replace
1-(4-(10-(phenylanthracene-9-base) phenyl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-base) benzene
Base)-1H-benzo [d] imidazoles, remaining step is all identical with the synthetic method described in embodiment 1, it is thus achieved that 4.87g product
(EX12), productivity is 66%.MS(m/z,FAB+): 902.8；1H NMR(CDCl3, 500MHz): chemistry
Displacement (ppm) 8.70 (d, 2H), 8.51 (d, 2H), 8.22 (s, 1H), 8.16～8.09 (d, 2H), 7.88～7.83 (m, 4H),
7.80～7.70 (m, 6H), 7.65～7.51 (m, 14H), 7.47～7.41 (m, 2H), 7.40～7.28 (m, 9H).
Produce the conventional method of organic el device
According to the present invention, it is provided that a kind of glass being coated with through indium tin oxide (indium tin oxide, ITO) is (hereafter
ITO base material), its resistance be 9 ohm-sq (ohm/square) to 12 ohm-sq and thickness be that 120nm arrives
160nm, and utilize multiple cleaning (such as: cleaning agent, deionized water) to be cleaned in ultrasonic bath.
Before the vapor deposition processes carrying out organic layer, by UV and ozone process further cleaned after ITO base material.
All pretreatment process for ITO base material are all carried out in toilet's (100 grades) environment.
Fine vacuum unit (10 at such as resistance heated quartz boat (resistively heated quartz boats) etc.-7Torr)
In, by vapour deposition, these organic layers are sequentially coated on ITO base material.Pass through quartz crystal monitor
(quartz-crystal monitor) accurately monitors or sets thickness and the vapor deposition rate (0.1nm/sec of respective layer
To 0.3nm/sec).As it has been described above, indivedual layers are also possible to be made up of more than one compounds, imply that and in general mix
The miscellaneous material of main part having dopant material.This types of material can be by carrying out common gasification from two or more source
(co-vaporization) reach.
Two pyrazines also [2,3-f:2,3-] quinoxaline-2,3,6,7,10,11-pregnancy nitrile (Dipyrazino [2,3-f:2,3-]
Quinoxaline-2,3,6,7,10,11-hexacarbonitrile, HAT-CN) in organic el device, can be used as electricity
Hole implanted layer.Double (the phenyl)-benzidine of double (naphthalene-1-the base)-N, N-of N, N-(N, N-Bis (naphthalene-1-yl)-
N, N-bis (phenyl)-benzidine, NPB) the most frequently used it is used as electricity hole transport layer.With reference to US 8,962,160 patent
Case, 10,10-dimethyl-12-(4-(pyrene-1-base) phenyl)-10H-indeno [1,2-b] triphenylene (10,10-Dimethyl-12-(4-
(pyren-1-yl) phenyl)-10H-indeno [1,2-b] triphenylene, PT-312) can be used as blue light emitting main body
(blue emitting host), and N1, tetra-tolyl pyrene-1 of N1, N6, N6-, 6-diamidogen
(N1, N1, N6, N6-tetramtolylpyrene-1,6-diamine) (D1) can be used as blue light object (blue guest).One
In embodiment, organic el device uses 2-(10,10-dimethyl-10H-indeno [2,1-B] triphenylene-13-base)-4,6-bis-
Phenyl-1,3,5-triazine (2-(10,10-dimethyl-10H-indeno [2,1-b] triphenylen-13-yl)-4,6-diphenyl-
1,3,5-triazine) (HB1), 2-(10,10-dimethyl-10H-indeno [2,1-B] triphenylene-12-base)-4,6-diphenyl-1,3,5-
Triazine (2-(10,10-dimethyl-10H-indeno [2,1-b] triphenylen-12-yl)-4,6-diphe-nyl-1,3,5-triazine)
(HB2) and general formula HB3 as electricity hole barrier material (HBM), 4,7-diphenyl-2-(4-(1-phenyl-1H-
Benzo [d] imidazoles-2-base) phenyl)-1,10-coffee quinoline (4,7-diphenyl-2-(4-(1-phenyl-1H-benzo [d]
Imidazol-2-yl) phenyl)-1,10-phenanthroline) (ET1), 2,9-bis-(naphthalene-2-base)-4,7-diphenyl-1,10-coffee quinoline
(2,9-di (naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline) (ET2) is used as electric transmission material
Material (ETM) with 5% lithium metal (Li) or 8-hydroxyquinoline ester group-lithium (8-hydroxyquinolato-lithium, LiQ)
Carry out co-depositing (co-deposition).For producing the OLED of the prior art of standard organic el device control group
Material and the present invention are for comparing the material of prior art, and its chemical constitution is as follows:
Typical organic el device is by the low workfunction metal institute structure of such as Al, Mg, Ca, Li, K or a combination thereof
Becoming, and become negative electrode by heat evaporation mode, low workfunction metal can be injected into electron transfer layer from negative electrode by auxiliary electron.
Additionally, in order to reduce the barrier that electronics injects, and improve organic el device performance, in negative electrode and electric transmission
Thin film electronic implanted layer is introduced between Ceng.The conventional material of electron injecting layer be have low work function metal halide or
Metal-oxide, such as: LiF, LiQ, MgO or Li2O.On the other hand, after organic el device manufactures,
By using PR650 spectral scan spectrogrph (PR650 spectra scan spectrometer) to measure EL spectrum
(EL spec-tra) and CIE coordinate (CIE coordination).Additionally, utilize Keithley 2400 programmable to set
Meter voltage-to-current source (Keithley 2400 programmable voltage-current source) obtains current/voltage
(current/voltage), luminescence/voltage (luminescence/voltage) and the spy of yield/voltage (yield/voltage)
Property.The said equipment is to operate in room temperature (about 25 DEG C) and atmospheric pressure environments.
Embodiment 4
Use is similar to the program of above-mentioned conventional method, and generation has having of a blue-fluorescence of following two kinds of apparatus structures
Machine EL device, the first apparatus structure is ITO/HAT-CN (20nm)/NPB (110nm)/doping 5%D1
ETM (the 35nm)/Al (160nm) of PT-312 (30nm)/HBM/ doping 5%Li, the second apparatus structure is
The PT-312 (30nm) of ITO/HAT-CN (20nm)/NPB (110nm)/doping 5%D1/HBM/ codeposition 50%
The ETM (40nm) of LiQ/LiQ (1nm)/Al (160nm).Send out the organic el device test report of blue-fluorescence
I-V-B (when 1000 nits (nit)) and half-life, wherein the half-life was defined as 1000 as shown in table 1 and table 2
cd/m2Original intensity drop to time of half.
Table 1
Table 2
In the preferred embodiment of above organic el device test report (seeing table 1 and table 2), show compared to existing
There is the organic EL Material of technology, the conduct in organic el device of the coffee quinoline derivant shown in formula (I) in the present invention
When electricity hole stops electron transport material or electron transport material, the most excellent characteristic can be shown.More particularly,
On the one hand, the organic el device of the present invention uses the coffee quinoline derivant shown in this formula (I) as electron transport material
With aforesaid electricity hole barrier material such as HB1, HB2 or HB3 time collocation use time, can show low power consumption,
High efficiency and long half-lift；Additionally, on the other hand, described coffee quinoline derivant can act also as electricity hole and stops electronics
Transmission material, and without using with the barrier material collocation of electricity hole, can show the best compared with the material of prior art equally
Good performance.
In sum, the present invention relates to a kind of coffee quinoline derivant, it has the structure as shown in formula (I), and permissible
Electron transport material or electron transport material is stopped as the electric hole in organic el device.The knot of aforementioned coffee quinoline derivant
Structure is to represent with following formula (I):
Wherein L represents the arlydene being substituted or being unsubstituted with 6 to 30 ring carbon atoms；M represents 0
To the integer of 6, n represents the integer of 0 to 4, and p represents the integer of 0 to 4；Ar is for having 6 to 50 ring carbon
The aryl being substituted or being unsubstituted of atom, aforesaid aryl can be phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, bend
Base or other alternative group；R1To R4Represent independently hydrogen atom, have 1 to 20 carbon atom through taking
Generation or the alkyl, the aryl being substituted or being unsubstituted with 6 to 30 carbon atoms that are unsubstituted or have 3
The heteroaryl being substituted or being unsubstituted to 30 carbon atoms.
The above is only presently preferred embodiments of the present invention, not has any pro forma restriction to the present invention, though
So the present invention relates to as above with preferred embodiment, but is not limited to the present invention, in any art
Technical staff, in the range of without departing from technical solution of the present invention, when the available above-mentioned technology contents related to is made
Permitted to change or modify the Equivalent embodiments of equivalent variations, as long as being the content without departing from technical solution of the present invention, according to this
Any simple modification, equivalent variations and the modification that above example is made by the technical spirit of invention, all still falls within this
In the range of bright technical scheme.
Claims (10)
1. a coffee quinoline derivant, it has a structure shown in following formula (I):
Wherein L represents the arlydene being substituted or being unsubstituted with 6 to 30 ring carbon atoms；M represents 0
To the integer of 6, n represents the integer of 0 to 4, and p represents the integer of 0 to 4；Ar is for having 6 to 50 ring carbon
The phenyl being substituted or being unsubstituted of atom, naphthyl, anthryl, phenanthryl, pyrenyl or chrysenyl；R1To R4Independently
Selected from the alkyl being substituted or being unsubstituted that by hydrogen atom, there is 1 to 20 carbon atom, have 6 to 30
The aryl being substituted or being unsubstituted of individual carbon atom and there is being substituted or without taking of 3 to 30 carbon atoms
The group that the heteroaryl in generation is formed.
2. coffee quinoline derivant as claimed in claim 1, wherein Ar has selected from the group being made up of general formula
A kind of structure in group:
3. coffee quinoline derivant as claimed in claim 1, wherein said derivant has a structure shown in following formula (II):
Wherein L represents the arlydene being substituted or being unsubstituted with 6 to 30 ring carbon atoms；M represent 0 to
The integer of 6, n represents the integer of 0 to 4, and p represents the integer of 0 to 4；Ar is former for having 6 to 50 ring carbon
The phenyl being substituted or being unsubstituted of son, naphthyl, anthryl, phenanthryl, pyrenyl or chrysenyl；R1To R4Independently
Selected from the alkyl being substituted or being unsubstituted that by hydrogen atom, there is 1 to 20 carbon atom, there are 6 to 30
The aryl being substituted or being unsubstituted of carbon atom and there is being substituted or being unsubstituted of 3 to 30 carbon atoms
The group that formed of heteroaryl.
4. coffee quinoline derivant as claimed in claim 3, wherein Ar has selected from the group being made up of general formula
A kind of structure in group:
5. the coffee quinoline derivant as according to any one of claim 1-4, the structure of wherein said coffee quinoline derivant by under
Shown in one of which in the group that row formula is formed:
6. an OLED, it includes pair of electrodes and at least one material layer, described to electrode by the moon
Pole and anode are formed, and described at least one material layer includes coffee quinoline derivant as claimed in claim 1 and is arranged at
Described to electrode between.
7. OLED as claimed in claim 6, wherein said at least one material layer is electron transfer layer.
8. OLED as claimed in claim 6, wherein said at least one material layer is that electricity hole stops electricity
Sub-transport layer.
9. the OLED as according to any one of claim 6-8, it farther includes an electricity hole and stops
Layer, and described electricity barrier layer, hole includes selected from the group that is made up of the compound of structure shown in general formula
Plant or multiple:
10. OLED as claimed in claim 7, wherein said electron transfer layer farther include lithium,
8-hydroxyquinoline-lithium or a combination thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/686,794 US9692003B2 (en) | 2015-04-15 | 2015-04-15 | Phenanthroline derivative and use thereof |
| US14/686,794 | 2015-04-15 |
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| CN106866660A (en) * | 2017-02-15 | 2017-06-20 | 上海天马有机发光显示技术有限公司 | Electron transport material, the OLED display panel comprising it and electronic equipment |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050236980A1 (en) * | 2002-07-10 | 2005-10-27 | Lecloux Daniel D | Charge transport compositions and electronic devices made with such compounds |
| US7282586B1 (en) * | 2006-08-11 | 2007-10-16 | Luminescence Technology Corp. | Dipyridine-based compound and the use thereof |
| US20080265746A1 (en) * | 2007-04-25 | 2008-10-30 | Feng Wen Yen | Phenanthroline compound and organic light emitting device using the same |
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| JP4261855B2 (en) * | 2002-09-19 | 2009-04-30 | キヤノン株式会社 | Phenanthroline compound and organic light emitting device using the same |
| US7629060B2 (en) * | 2002-11-26 | 2009-12-08 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, and display and illuminator |
| CN101010404B (en) | 2004-08-23 | 2010-08-11 | 东丽株式会社 | Material for luminous component and luminous component |
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2015
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050236980A1 (en) * | 2002-07-10 | 2005-10-27 | Lecloux Daniel D | Charge transport compositions and electronic devices made with such compounds |
| US7282586B1 (en) * | 2006-08-11 | 2007-10-16 | Luminescence Technology Corp. | Dipyridine-based compound and the use thereof |
| US20080265746A1 (en) * | 2007-04-25 | 2008-10-30 | Feng Wen Yen | Phenanthroline compound and organic light emitting device using the same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866660A (en) * | 2017-02-15 | 2017-06-20 | 上海天马有机发光显示技术有限公司 | Electron transport material, the OLED display panel comprising it and electronic equipment |
| CN106866660B (en) * | 2017-02-15 | 2019-05-17 | 上海天马有机发光显示技术有限公司 | Electron transport material, OLED display panel and electronic equipment comprising it |
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| TWI555749B (en) | 2016-11-01 |
| TW201636349A (en) | 2016-10-16 |
| CN106045990B (en) | 2017-12-01 |
| US9692003B2 (en) | 2017-06-27 |
| US20160308159A1 (en) | 2016-10-20 |
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